The first message was relatively innocuous, but the ones that followed became weren’t – he was making the kind of jokes-but-not-really that assume a greater level of familiarity between the two than actually existed.
Two people who had at least a passing relationship online might get away with tweets like “For my birthday, I want @gracespelman to follow me back”; from a complete stranger, that’s just unsettlingly creepy.
One of the hard and fast rules of dating and not being creepy is recognizing that everybody has boundaries and those boundaries are flexible; some people have greater levels of access to us than others because we have different levels of intimacy with them.
One of the keys of what makes somebody creepy is very simple: creepers assume a greater level of intimacy than actually exists.
Someone who is socially well-calibrated can get away with more than someone approaches; the odds are against you and you can end up making yourself seem creepy when you don’t intend to.
Approaching people you don’t know and have no connection to means that you have to behave accordingly.